ES2386796T3 - Derivados de urea cíclicos sustituidos y su utilización como moduladores del receptor vainilloide 1 - Google Patents
Derivados de urea cíclicos sustituidos y su utilización como moduladores del receptor vainilloide 1 Download PDFInfo
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- ES2386796T3 ES2386796T3 ES06742597T ES06742597T ES2386796T3 ES 2386796 T3 ES2386796 T3 ES 2386796T3 ES 06742597 T ES06742597 T ES 06742597T ES 06742597 T ES06742597 T ES 06742597T ES 2386796 T3 ES2386796 T3 ES 2386796T3
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- butyl
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- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical class OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 108010062740 TRPV Cation Channels Proteins 0.000 title description 12
- 102000011040 TRPV Cation Channels Human genes 0.000 title description 11
- -1 methylenedioxy group Chemical group 0.000 claims abstract description 118
- 125000001424 substituent group Chemical group 0.000 claims abstract description 92
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 76
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 70
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 63
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 51
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 45
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 37
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 25
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 246
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 144
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 134
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 97
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 94
- 239000000203 mixture Substances 0.000 claims description 89
- 239000000460 chlorine Substances 0.000 claims description 77
- 239000012429 reaction media Substances 0.000 claims description 73
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 70
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Inorganic materials [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 57
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 56
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 55
- 239000003814 drug Substances 0.000 claims description 54
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 54
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 54
- 208000002193 Pain Diseases 0.000 claims description 53
- 239000002585 base Substances 0.000 claims description 53
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 52
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 50
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 46
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 45
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 42
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 38
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 35
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 34
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 32
- 229940079593 drug Drugs 0.000 claims description 30
- 230000036407 pain Effects 0.000 claims description 30
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 29
- 239000012453 solvate Substances 0.000 claims description 29
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 23
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims description 22
- 108010025083 TRPV1 receptor Proteins 0.000 claims description 21
- 229910052987 metal hydride Inorganic materials 0.000 claims description 21
- 239000011591 potassium Substances 0.000 claims description 20
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 20
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 19
- 235000009518 sodium iodide Nutrition 0.000 claims description 19
- 208000007848 Alcoholism Diseases 0.000 claims description 18
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 18
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 18
- 206010013663 drug dependence Diseases 0.000 claims description 18
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 18
- 208000011117 substance-related disease Diseases 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 239000012312 sodium hydride Substances 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 201000009032 substance abuse Diseases 0.000 claims description 13
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims description 12
- 125000006023 1-pentenyl group Chemical group 0.000 claims description 12
- 125000006017 1-propenyl group Chemical group 0.000 claims description 12
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 12
- 125000006024 2-pentenyl group Chemical group 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 12
- 208000000094 Chronic Pain Diseases 0.000 claims description 12
- 206010020853 Hypertonic bladder Diseases 0.000 claims description 12
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 12
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 12
- 206010048010 Withdrawal syndrome Diseases 0.000 claims description 12
- 201000007930 alcohol dependence Diseases 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 208000004296 neuralgia Diseases 0.000 claims description 12
- 208000021722 neuropathic pain Diseases 0.000 claims description 12
- 208000020629 overactive bladder Diseases 0.000 claims description 12
- 238000011321 prophylaxis Methods 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 208000005298 acute pain Diseases 0.000 claims description 11
- 229960002504 capsaicin Drugs 0.000 claims description 11
- 235000017663 capsaicin Nutrition 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- MKTBNEVNQZSLKZ-UHFFFAOYSA-N n-[4-[[2-oxo-3-[[4-(trifluoromethoxy)phenyl]methyl]benzimidazol-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CN1C(=O)N(CC=2C=CC(OC(F)(F)F)=CC=2)C2=CC=CC=C21 MKTBNEVNQZSLKZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 10
- 206010046543 Urinary incontinence Diseases 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000002671 adjuvant Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 238000011161 development Methods 0.000 claims description 8
- CQHFJJKPVBEQPR-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-oxo-1,3-diazinan-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=O)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)CCC1 CQHFJJKPVBEQPR-UHFFFAOYSA-N 0.000 claims description 8
- WBCBMZUWDPQZTE-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-oxoimidazolidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=O)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)CC1 WBCBMZUWDPQZTE-UHFFFAOYSA-N 0.000 claims description 8
- SFBOPJGETMJNNI-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-sulfanylidenebenzimidazol-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=S)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)C2=CC=CC=C21 SFBOPJGETMJNNI-UHFFFAOYSA-N 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
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- 125000002541 furyl group Chemical group 0.000 claims description 7
- PBSTZASQOWSHIK-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-sulfanylideneimidazolidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=S)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)CC1 PBSTZASQOWSHIK-UHFFFAOYSA-N 0.000 claims description 7
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
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- 238000002483 medication Methods 0.000 claims description 6
- OSQQLFDMRLVXNW-UHFFFAOYSA-N n-[4-[[2-sulfanylidene-3-[[4-(trifluoromethoxy)phenyl]methyl]benzimidazol-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CN1C(=S)N(CC=2C=CC(OC(F)(F)F)=CC=2)C2=CC=CC=C21 OSQQLFDMRLVXNW-UHFFFAOYSA-N 0.000 claims description 6
- YQCAHQCLQBFUAR-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-oxobenzimidazol-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=O)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)C2=CC=CC=C21 YQCAHQCLQBFUAR-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 5
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims description 5
- OUEKLNJUMVZULZ-UHFFFAOYSA-N 2-[4-(2-aminoethoxy)-3-methoxyphenyl]-n-[3-(3,4-dimethylphenyl)propyl]acetamide;hydron;chloride Chemical compound Cl.C1=C(OCCN)C(OC)=CC(CC(=O)NCCCC=2C=C(C)C(C)=CC=2)=C1 OUEKLNJUMVZULZ-UHFFFAOYSA-N 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
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- 125000003725 azepanyl group Chemical group 0.000 claims description 5
- 210000000748 cardiovascular system Anatomy 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
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- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 5
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- RLWGDRLXZSLGHV-UHFFFAOYSA-N 1-[[4-(2-aminoethoxy)-3-methoxyphenyl]methyl]-3-[(4-tert-butylphenyl)methyl]urea Chemical compound C1=C(OCCN)C(OC)=CC(CNC(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1 RLWGDRLXZSLGHV-UHFFFAOYSA-N 0.000 claims description 4
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- IKYCZSUNGFRBJS-UHFFFAOYSA-N Euphorbia factor RL9 = U(1) = Resiniferatoxin Natural products COC1=CC(O)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 IKYCZSUNGFRBJS-UHFFFAOYSA-N 0.000 claims description 4
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- OPZKBPQVWDSATI-KHPPLWFESA-N N-Vanillyloleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 OPZKBPQVWDSATI-KHPPLWFESA-N 0.000 claims description 4
- QVLMCRFQGHWOPM-ZKWNWVNESA-N N-arachidonoyl vanillylamine Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC1=CC=C(O)C(OC)=C1 QVLMCRFQGHWOPM-ZKWNWVNESA-N 0.000 claims description 4
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005018191 | 2005-04-19 | ||
| DE102005018191A DE102005018191A1 (de) | 2005-04-19 | 2005-04-19 | Substituierte zyklische Harnstoff-Derivate und deren Verwendung zur Herstellung von Arzneimitteln |
| PCT/EP2006/003519 WO2006111346A1 (de) | 2005-04-19 | 2006-04-18 | Substituierte zyklische harnstoff-derivate und deren verwendung als vanilloid-rezeptor 1 modulatoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2386796T3 true ES2386796T3 (es) | 2012-08-30 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| ES06742597T Active ES2386796T3 (es) | 2005-04-19 | 2006-04-18 | Derivados de urea cíclicos sustituidos y su utilización como moduladores del receptor vainilloide 1 |
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| Country | Link |
|---|---|
| US (1) | US8207182B2 (de) |
| EP (1) | EP1874733B1 (de) |
| JP (1) | JP5214436B2 (de) |
| CA (1) | CA2605144C (de) |
| DE (1) | DE102005018191A1 (de) |
| ES (1) | ES2386796T3 (de) |
| PL (1) | PL1874733T3 (de) |
| WO (1) | WO2006111346A1 (de) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2008029168A2 (en) * | 2006-09-08 | 2008-03-13 | Summit Corporation Plc | Treatment of duchenne muscular dystrophy |
| CN101925575B (zh) | 2008-01-28 | 2014-06-18 | 株式会社爱茉莉太平洋 | 作为香草酸受体拮抗剂的化合物、其异构体或其药物学可接受的盐、及包含这些化合物的药物组合物 |
| WO2010002209A2 (en) | 2008-07-02 | 2010-01-07 | Amorepacific Corporation | Novel compounds, isomer thereof, or pharmaceutically acceptable salts thereof as vanilloid receptor antagonist and pharmaceutical compositions containing the same |
| EP2464631A1 (de) * | 2009-08-12 | 2012-06-20 | Technion Research & Development Foundation Ltd. | Polycyclische verbindungen mit der bezeichnung calixurene und ihre verwendungen |
| US8815265B2 (en) | 2010-06-30 | 2014-08-26 | Avon Products, Inc. | Cosmetic use of N-substituted sulfonyloxybenzylamines and related compounds |
| JP7425537B2 (ja) * | 2016-10-06 | 2024-01-31 | 日産化学株式会社 | ジアミン、重合体、液晶配向剤、液晶配向膜及び液晶表示素子 |
| WO2022260016A1 (ja) * | 2021-06-07 | 2022-12-15 | 学校法人近畿大学 | Ｔ型カルシウムチャネル阻害剤 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE1670368A1 (de) * | 1966-07-16 | 1970-11-05 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung aralkylsubstituierter Lactame und Cyclischer Harnstoffe |
| JPS588503B2 (ja) * | 1974-12-27 | 1983-02-16 | 富士写真フイルム株式会社 | カラ−シヤシンカンコウザイリヨウ |
| JPS58203976A (ja) * | 1982-05-24 | 1983-11-28 | Sumitomo Chem Co Ltd | ベンズイミダゾリン−２−チオン誘導体の製造法 |
| JPS63170011A (ja) * | 1987-01-07 | 1988-07-13 | Mitsubishi Monsanto Chem Co | アミド系樹脂成形品およびその製造法 |
| GB8724912D0 (en) | 1987-10-23 | 1987-11-25 | Wellcome Found | Indole derivatives |
| DE4300912A1 (de) * | 1993-01-15 | 1994-07-21 | Merck Patent Gmbh | Chinazolinderivate |
| FR2722190B1 (fr) * | 1994-07-05 | 1996-10-04 | Sanofi Sa | Derives de 1-benzyl-1,3-dihydro-2h-benzimidazol-2-one, leur preparation, les compositions pharmaceutique en contenant |
| US5612363A (en) * | 1995-06-02 | 1997-03-18 | Berlex Laboratories, Inc. | N,N-di(aryl) cyclic urea derivatives as anti-coagulants |
| WO1997008150A1 (en) * | 1995-08-22 | 1997-03-06 | The Du Pont Merck Pharmaceutical Company | Substituted cyclic ureas and derivatives thereof useful as retroviral protease inhibitors |
| EP1303483B1 (de) * | 2000-08-21 | 2008-04-23 | Pacific Corporation | Neue thiourea-derivate und pharmazeutische zusammensetzungen die diese enthalten |
| WO2004103281A2 (en) * | 2003-05-16 | 2004-12-02 | Georgetown University | Vanilloid receptor antagonists, and methods of making and using them |
| JPWO2006104280A1 (ja) | 2005-03-31 | 2008-09-11 | 武田薬品工業株式会社 | 糖尿病の予防・治療剤 |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1874733A1 (de) | 2008-01-09 |
| JP5214436B2 (ja) | 2013-06-19 |
| CA2605144A1 (en) | 2006-10-26 |
| JP2008538366A (ja) | 2008-10-23 |
| CA2605144C (en) | 2014-05-27 |
| DE102005018191A1 (de) | 2006-10-26 |
| WO2006111346A1 (de) | 2006-10-26 |
| US20080090855A1 (en) | 2008-04-17 |
| PL1874733T3 (pl) | 2012-09-28 |
| EP1874733B1 (de) | 2012-06-20 |
| US8207182B2 (en) | 2012-06-26 |
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